In my car on the way back and forth between Denver and Boulder the past few days, I listened to The Steve Ballmer Interview on the Acquired podcast by Ben Gilbert and David Rosenthal. If you aren’t a subscriber, it’s in the category of a “must-listen to podcast.” I’ve known Ben and David for many years from their time at PSL and Madrona, and they’ve created an outstanding new media property with Acquired.
While their two-part series on Microsoft (Microsoft Volume I and Microsoft Volume II) is excellent, The Steve Ballmer Interview is extraordinary.
While I doubt Steve ever thinks of me, I have enormous respect for him. I met him for the first time in the early 1990s on a trip to Microsoft when I was running my first company (Feld Technologies). Dwayne Walker had organized an event for the early group of Microsoft Solution Providers, and we were one of them. It was the first time I had been on the Microsoft campus, which was growing like crazy. Steve spoke at one of the events and I got to shake his hand. I was the President (we didn’t have a CEO) of this tiny little company in Boston, and I was in awe of him.
The next time I met him was after AmeriData acquired Feld Technologies. My company had become the consulting division (AmeriData Consulting), I was the CTO, and on the deal team. AmeriData was the largest Novell NetWare reseller in the world, and Microsoft was working hard to get us to be a significant Windows NT Server reseller. AmeriData and Microsoft held a day-long meeting that included approximately a dozen AmeriData leaders and an equal number of Microsoft leaders. I was part of the AmeriData delegation, and Steve was standing at the head of a very long table. As people went around the room introducing themselves, he stopped at me and said, “Is your dad Charlie Feld?” I responded with “He’s my uncle.” Steve, in his thunderous voice, said, “That guy is single-handedly keeping OS/2 alive!” My AmeriData colleagues were likely uncomfortable and regretted that I came. Steve then laughed and said, “Tell Charlie hello.”
In the mid-2000s, after the internet bubble had collapsed, Dan’l Lewin organized a group of VCs that included me to be part of a Microsoft VC Advisory board. We had quarterly meetings with different teams at Microsoft as they attempted to win back the hearts and minds of VCs and the developer community, who had turned against them aggressively during and after the internet bubble. We split our meetings between Redmond and the Microsoft office in the Bay Area.
These were fun meetings where, with Scott Maxwell, the two of us endlessly played the role of provocateur because neither of us needed anything from Microsoft, couldn’t restrain ourselves, and just had fun riffing off each other. Dan’l encouraged us with setups like, “Brad and Scott, please, no BS today, just tell us why we are going to get our clocks cleaned in Mobile by Apple now that the iPhone is out.” Or, “Please tell us what is wrong with Project Red Dog when compared to AWS.”
I recall Steve attending at least one of these, and Scott Guthrie serving as a proxy for Steve at another one. They were rambunctious and fun. Steve was trying to convince us of the Windows three-screens and the cloud strategy, and Maxwell and I pulled out our iPhones and said, “Nope – not gonna happen.” (The three-screens part didn’t, but the cloud part did.)
Even though Steve made a lot of mistakes, he was super clear about what his strategy was and how he was trying to get this huge company to shift and move and dodge and evolve and survive in what is one of the roughest markets ever for incumbents. I adored his energy, his willingness to debate and keep searching for answers, and his ability to engage deeply with people, even when they challenged every aspect of what he was doing. Oh, and his boisterous and self-depricating personality.
You’ll feel the same energy and intellect from Steve in this episode, including deep discussions about things he got wrong. And, even though he has been extraordinarily successful, you can hear his humility come through in how he discusses his experiences—good and bad—with his incredible journey at Microsoft spanning over 34 years.